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【结 构 式】

【药物名称】MRS-2179

【化学名称】2'-Deoxy-N6-methyladenosine-3',5'-bisphosphate

【CA登记号】

【 分 子 式 】C11H17N5O9P2

【 分 子 量 】425.23384

【开发单位】Natl. Inst. Health, Bethesda, MD (US); Univ. North Carolina, Chapel Hill, NC (US)

【药理作用】PHARMACOLOGICAL TOOLS

合成路线1

2'-Deoxyadenosine (I) was protected as the diacetate (II) on treatment with acetic anhydride and a catalytic amount of dimethylaminopyridine. Then, reaction with an excess of isopentyl nitrite and diiodomethane under illumination of a tungsten lamp provided iodide (III). Subsequent treatment with ethanolic methylamine effected both deacetylation and substitution of iodide to give 2'-deoxy-N6-methyladenosine (IV). Finally, this was treated with phosphoryl chloride and Proton Sponge(R) in trimethyl phosphate at 0 C, followed by quenching with triethyl ammonium bicarbonate buffer to yield the target bisphosphate.

1 Camaioni, E.; et al.; Deoxyadenosine bisphosphate derivatives as potent antagonists at P2Y1 receptors. J Med Chem 1998, 41, 1, 183-190.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18061 (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydro-3-furanol 958-09-8 C10H13N5O3 详情 详情
(II) 18062 [(2R,3S,5R)-3-(acetoxy)-5-(6-amino-9H-purin-9-yl)tetrahydro-2-furanyl]methyl acetate C14H17N5O5 详情 详情
(III) 18063 [(2R,3S,5R)-3-(acetoxy)-5-(6-iodo-9H-purin-9-yl)tetrahydro-2-furanyl]methyl acetate C14H15IN4O5 详情 详情
(IV) 18064 N6-Methyl-2'-deoxyadenosine; (2R,3S,5R)-2-(hydroxymethyl)-5-[6-(methylamino)-9H-purin-9-yl]tetrahydro-3-furanol 2002-35-9 C11H15N5O3 详情 详情
Extended Information